The present invention relates to a novel N-[2-(pyridyl)propyl]-N-substituted sulfonamide, a herbicide containing the same as an active ingredient and an intermediate thereof. More particularly, the present invention relates to an N-[2-(pyridyl)propyl]-N-substituted sulfonamide represented by the following general formula (I): ##STR2## wherein J represents a phenyl group which may be substituted or benzo-condensed, A represents --CH.sub.2 --, --CH.dbd.CH--, --O-- or --N(r)-- (wherein r represents an alkyl group having 1 to 4 carbon atoms), b represents 0 or 1, R represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a fluoroalkyl group or a formyl group, D represents a hydroxyl group, E represents a halogen atom, an alkylsulfonyloxy group or a benzenesulfonyloxy group which may be substituted or D and E represent --O-- in combination, and V represents a pyridyl group which may be substituted, a herbicide containing said N-[2-(pyridyl)propyl]-N-substituted sulfonamide as an active ingredient and a 1-(halogenomethyl)vinylpyridine as an intermediate thereof.
Many sulfonamide compounds have conventionally been proposed as a herbicide. For example, Japanese Patent Publication No. 56-8027 (1981) discloses N-methyl-N-.alpha.,.alpha.-dimethylbenzylbenzenesulfonamide. The present inventors have proposed N-(2,3-epoxypropylene)-N-aralkylsulfonamides such as N-(2,3-epoxypropylene)-N-.alpha.-methylbenzylbenzene sulfonamide [Japanese Patent Application Laid-Open (KOKAI) No. 58-131977 (1983)] as a selective herbicide. Japanese Patent Application Laid-Open (KOKAI) Nos. 57-32267 (1982) and 61-286366 (1986) disclose sulfonamides having a pyridyl group as a compound having a herbicidal activity or a fungicidal activity.
On the other hand, 1-(halogenomethyl)vinylpyridines in the present invention are novel compounds which have not been reported in any publication. As the related arts to 1-(halogenomethyl)vinylpyridines of the present invention, for example, L. F. Hatch and T. L. Patton, J. Am. Chem. Soc., 76, 2705 (1954) disclose a method of preparing 3-chloro (or 3-bromo)-2-phenylpropene; M. G. Voronkov, et al, Zh. Org. Khim., 8(11) 2347(1972) disclose a method of producing 3-chloro-2-(4-methylphenyl)propene; U. K. Pandit and H. Bieraugel, Recl. Trav. Chim. Pays-Bas, 95(9) 223(1976) disclose 3-bromo-2-(3-methoxyphenyl)propene as an intermediate for the synthesis of 6-methyl-19-norsteroid; European Patent Application No. 94167A discloses 3-bromo-2-(4-chlorophenyl)propene as an intermediate for the production of an azole fungicide; and V. V. Dhekne et al, Indian J. Chem. Sect. B, 19B(3) 188(1980) describe a method of preparing 3-bromo-2-(2-methoxy-4-methylphenyl)propene.
As 1-(substituted methyl)vinylpyridines described in publications, 2-(1-hydroxy (or acetoxy) methylvinyl)pyridine [Acta Chim. Scand. Ser. B, B29 (10) 985(1975) and Prom-st. Sint. Kauch, 1978 (8)2]; 4-(1-hydroxymethylvinyl)pyridine and 2-(1-hydroxymethylvinyl)-6-methylpyridine [Prom-st. Sint. Kauch 1978 (8)2]; 2-[1-(N,N-diethylaminomethyl)vinyl]-5-vinylpyridine [Khim. Geterotsikl. Soedin., 1968 (1) 128]; 4-(1-trimethylsilylmethylvinyl)pyridine [Bull. Chem. Soc. Jpn., 57(7), 1994 (1984)], etc. are known. All of these are, however, unsuitable as an intermediate for producing a sulfonamide having a herbicidal activity in accordance with the present invention in the respect of the reactivity.
Accordingly, it is desired to provide a herbicide which has a higher herbicidal activity than a conventional known sulfonamide compound and has a continuous herbicidal activity on weeds such as Echinochloa crus-galli in a long period from before the germination to an advanced stage of growing.
As a result of the studies undertaken by the present inventors, it has been found that N-[2-(pyridyl)propyl]-N-substituted sulfonamides represented by the following general formula (I): ##STR3## wherein J represents a phenyl group which may be substituted or benzo-condensed, A represents --CH.sub.2 --, --CH.dbd.CH--, --O-- or --N(r)-- (wherein r represents an alkyl group having 1 to 4 carbon atoms), b represents 0 or 1, R represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a fluoroalkyl group or a formyl group, D represents a hydroxyl group, E represents a halogen atom, an alkylsulfonyloxy group or a benzenesulfonyloxy group which may be substituted, or D and E represent --O-- in combination, and V represents a pyridyl group which may be substituted, have a very strong herbicidal effect on Echinochloa crus-galli from before the germination to an advanced stage of growing and cause little damage to paddy-rice plants. On the basis of this finding, the present invention has been achieved.